Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones.
Pritchard, R.P. Sheldrake, Helen M. Taylor, I.Z. Wallace, T.W.
Pritchard, R.P.
Sheldrake, Helen M.
Taylor, I.Z.
Wallace, T.W.
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2008-06-23
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Abstract
The tetracyclic nucleus of puupehenone, 15-oxopuupehenol and other sesquiterpene¿phenol natural
products can be assembled stereoselectively in three steps, the last of these being the 6-endo-trig cyclisation
of an alpha-keto radical generated from a substituted 2-(2-cyclohexenyl)ethyl 3-bromo-4-chromanone under metal-free conditions.
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Pritchard, R. G., Sheldrake, H. M., Taylor, I. Z. and Wallace, T. W. (2008). Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones. Tetrahedron Letters, Vol. 49, pp. 4156-4159.
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